Real Estate Investment Properties for Sale in Longwood, FL
Looking for investment property in Longwood, FL with high ROI ?
Explore a variety of short-term homes & houses in Longwood, FL. Invest wisely with VRBO & Longwood, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Longwood, FL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
12 HORSEMAN COVELongwood, FLAverage monthly electric bill is $35.00 Welcome to this incredible opportunity in the ... |
4 beds | 2 baths | 2,265 sq.ft. |
$524,999 |
Airbnb cash on cash: 6.87%
|
4102 CLUBSIDE DRIVE #4102Longwood, FLSpacious 2-Bedroom Corner Unit in Clubside at Sabal Point â Private, Updated & Move-In R... |
2 beds | 3 baths | 1,380 sq.ft. |
$240,000 |
Airbnb cash on cash: -1.28%
|
401 REIDER AVENUELongwood, FLLakefront living in the heart of Longwood! This charming 3-bedroom, 2-bath home is situate... |
3 beds | 2 baths | 1,451 sq.ft. |
$429,000 |
Airbnb cash on cash: 4.32%
|
2086 JUDITH PLACELongwood, FLUnder contract-accepting backup offers. ***Multiple offers have been made. Seller is reque... |
4 beds | 2 baths | 2,763 sq.ft. |
$714,900 |
Airbnb cash on cash: 4.77%
|
104 AUTUMN DRIVELongwood, FLThis beautifully updated townhome in Longwoodâs coveted Springs community offers a seren... |
2 beds | 2 baths | 1,839 sq.ft. |
$444,000 |
Airbnb cash on cash: -0.68%
|
211 FAIRWAY DRIVE #211Longwood, FLWelcome to this charming condo located in the highly sought-after, gated community of The ... |
3 beds | 2 baths | 1,496 sq.ft. |
$200,000 |
Airbnb cash on cash: 7.2%
|
204 TOMOKA TRAIL #204Longwood, FLWelcome to this stunning two-story condo located in the premier, guard-gated community of ... |
2 beds | 2 baths | 1,599 sq.ft. |
$248,000 |
Airbnb cash on cash: -0.91%
|
115 TOMOKA TRAIL #115Longwood, FLOne or more photo(s) has been virtually staged. One or more photo(s) has been virtually st... |
3 beds | 2 baths | 1,590 sq.ft. |
$289,000 |
Airbnb cash on cash: 6.25%
|
641 E CHURCH AVENUELongwood, FLReady to save money on gas, your utility bills and home maintenance ? Welcome home to 641 ... |
3 beds | 2 baths | 1,537 sq.ft. |
$365,000 |
Airbnb cash on cash: 5.59%
|
112 CROWN OAKS WAY #112Longwood, FLOwner financing available for this condo! WELCOME TO THE SPRINGS! - A GUARD-GATED COMMUNIT... |
2 beds | 2 baths | 1,119 sq.ft. |
$159,900 |
Airbnb cash on cash: -3.34%
|
205 HICKORY DRIVELongwood, FLBeautifully Updated Pool Home in Sweetwater Oaks! Welcome to this stunning 4-bedroom, 2-ba... |
4 beds | 2 baths | 1,867 sq.ft. |
$599,900 |
Airbnb cash on cash: 5.66%
|
2681 AZALEA DRIVELongwood, FLEnjoy the best of Longwood living in this charming 3-bedroom, 2-bath home on a spacious qu... |
3 beds | 2 baths | 1,399 sq.ft. |
$375,000 |
Airbnb cash on cash: 4.79%
|
945 NORFOLK COURTLongwood, FLThis is a charming 2 bedroom, 2 bathroom townhouse in the much desired Danbury Mill. A qua... |
2 beds | 2 baths | 1,402 sq.ft. |
$340,000 |
Airbnb cash on cash: -0.53%
|
364 HOWARD BOULEVARDLongwood, FLWelcome to this charming 3-bedroom, 2-bath home tucked away at the end of a quiet dead-end... |
3 beds | 2 baths | 1,400 sq.ft. |
$375,000 |
Airbnb cash on cash: 5.25%
|
102 FAIRWAY DRIVE #102Longwood, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. Do... |
1 beds | 1 baths | 884 sq.ft. |
$175,000 |
Airbnb cash on cash: 0.44%
|
182 CITRUS TREE LANELongwood, FLWelcome to this Charming, Beautifully Maintained 4-Bedroom, 2-Bath POOL Home located in th... |
4 beds | 2 baths | 1,759 sq.ft. |
$488,000 |
Airbnb cash on cash: 7.01%
|
310 VISTA OAK DRIVELongwood, FL~MOTIVATED SELLER~ Welcome to your dream home in the highly sought-after gated community... |
4 beds | 5 baths | 3,286 sq.ft. |
$999,500 |
Airbnb cash on cash: 2.33%
|
2815 SPYGLASS COVELongwood, FLWelcome to 2815 Spyglass Cove in beautiful Longwood, Florida. This fully updated 2-bedroom... |
2 beds | 2 baths | 1,158 sq.ft. |
$283,900 |
Airbnb cash on cash: -0.59%
|
3340 PARK GROVE COURTLongwood, FLElevated elegance meets exceptional design in this estate located on a premium cul-de-sac ... |
4 beds | 4 baths | 3,266 sq.ft. |
$1,299,000 |
Airbnb cash on cash: 1.3%
|
561 SHINING ARMOR LANELongwood, FLInvest with success and buy through Auction.com. This bank-owned investment property is a ... |
N/A beds | N/A baths | N/A |
$358,000 |
Airbnb cash on cash: 2.29%
|
2710 ENGLISH IVY CTLongwood, FLUnder contract-accepting backup offers. Welcome to this stunning 4-bedroom, 4-bathroom hom... |
4 beds | 4 baths | 4,219 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 1.89%
|
345 W HORNBEAM DRIVELongwood, FLExquisite Modern Renovation in Sabal Point! Welcome to this stunningly remodeled 4-bedroo... |
4 beds | 2 baths | 2,177 sq.ft. |
$634,900 |
Airbnb cash on cash: 5.42%
|
105 FAIRWAY DRIVELongwood, FLStunning 2-Bedroom Condo in Gated Community â Fairway Villas at The Springs! Welcome ... |
2 beds | 1 baths | 1,140 sq.ft. |
$205,000 |
Airbnb cash on cash: -1.57%
|
731 CRESTBROOK LOOPLongwood, FLWelcome to 731 Crestbrook Loop in The Landings- one of Longwoodâs most desirable gated ... |
3 beds | 3 baths | 2,140 sq.ft. |
$425,000 |
Airbnb cash on cash: 4.02%
|
2040 E TRIANGLE DRIVELongwood, FL**NEW PRICE REDUCTION!** Now priced below market value. Charming, Updated 3-Bedroom Home ... |
3 beds | 2 baths | 1,283 sq.ft. |
$350,000 |
Airbnb cash on cash: 5.33%
|
165 FIG TREE RUNLongwood, FLWelcome to 165 FIG TREE RUN, A Beautifully Updated Pool Home in the Gated Longwood Club Ne... |
4 beds | 2 baths | 2,121 sq.ft. |
$550,000 |
Airbnb cash on cash: 5.7%
|
358 WINCHESTER COURTLongwood, FLRenovated 3-bedroom, 2.5-bath townhome in Governorâs Point with kitchen and primary bath... |
3 beds | 3 baths | 1,682 sq.ft. |
$345,000 |
Airbnb cash on cash: 3.46%
|
258 W Sabal Palm Place #22Longwood, FLEnjoy low-maintenance living & a terrific investment opportunity! This stylish 2-bedroom, ... |
2 beds | 2 baths | 1,202 sq.ft. |
$257,500 |
Airbnb cash on cash: -1.65%
|
966 N RONALD REAGAN BOULEVARDLongwood, FLHIGH AND DRY! Located just 1/2 mile from the Longwood SunRail Station. Donât miss your o... |
5 beds | 3 baths | 2,490 sq.ft. |
$595,000 |
Airbnb cash on cash: N/A
|
4 HUDSON COVELongwood, FLFully Renovated 4-Bedroom Pool Home in the Heart of Central Florida. Welcome home! This... |
4 beds | 3 baths | 2,263 sq.ft. |
$579,999 |
Airbnb cash on cash: 5.77%
|
674 PINE SHADOW COURTLongwood, FLDiscover this beautifully maintained 4-bedroom, 3-bath home in the sought-after Sabal Poin... |
4 beds | 3 baths | 2,754 sq.ft. |
$710,000 |
Airbnb cash on cash: 4.75%
|
342 MAPLE DRIVELongwood, FLThis amazing, meticulously remodeled one-story pool home offers an exceptional location fa... |
4 beds | 3 baths | 2,799 sq.ft. |
$844,000 |
Airbnb cash on cash: 3.66%
|
179 CROWN POINT CIRCLELongwood, FLWelcome home to your gorgeous new Longwood condo in the highly desired community of Crown ... |
2 beds | 2 baths | 1,406 sq.ft. |
$249,000 |
Airbnb cash on cash: 0.87%
|
300 SPRING RUN CIRCLELongwood, FLShort Sale. Step into the lifestyle you've always dreamed of in the exclusive, guard gated... |
3 beds | 3 baths | 2,416 sq.ft. |
$524,900 |
Airbnb cash on cash: 3.05%
|
223 ROYAL OAKS CIRCLELongwood, FLIMPROVED PRICE! One of the BEST VALUES per square foot in Sweetwater Oaks! Welcome to one... |
4 beds | 2 baths | 2,842 sq.ft. |
$639,900 |
Airbnb cash on cash: 5.87%
|
1510 PELICAN STREETLongwood, FL3-bed, 2-bath residence nestled on a serene, tree-lined street in one of Longwoodâs DESI... |
3 beds | 2 baths | 1,269 sq.ft. |
$332,000 |
Airbnb cash on cash: 5.34%
|
154 GOLF CLUB DRIVE #154Longwood, FLNEW PRICE! and SELLER IS OFFERING HOA CREDIT - $500 PER MONTH FOR ONE YEAR ($6,000) with a... |
3 beds | 2 baths | 1,679 sq.ft. |
$369,000 |
Airbnb cash on cash: 3.15%
|
115 MARCY BOULEVARDLongwood, FLUnder contract-accepting backup offers. Welcome to 115 Marcy Blvd, a charming residence ne... |
5 beds | 3 baths | 2,013 sq.ft. |
$499,995 |
Airbnb cash on cash: N/A
|
453 E Jessup AvenueLongwood, FLFully Renovated Longwood Gem - Move-In Ready! Welcome to 453 E Jessup Ave, a beautifully r... |
2 beds | 1 baths | 864 sq.ft. |
$270,000 |
Airbnb cash on cash: 0.51%
|
722 EAGLE AVENUELongwood, FLInvestor Goldmine in Longwood! Attention flippers, rehabbers, and savvy investors â This... |
3 beds | 2 baths | 1,548 sq.ft. |
$299,000 |
Airbnb cash on cash: 6.04%
|
Real Estate investment in Longwood, FL
There are 141 properties for sale in the city of Longwood . The median list price in Longwood is $469,900 and the average price per square foot is $220. In September 2025, the average monthly cash on cash return in Longwood is 4.00%. The average monthly rental income in Longwood is $2,329.